Under Sail from Puglia to Sicily

Dubrovnik, Croatia's stunning port city, is a blend of rich history, dramatic architecture, and vibrant culture, making it a must-visit destination. Don't miss a stroll along the city walls for breathtaking views and savor local dishes like "peka" and "black risotto." The best time to visit is in late spring or early fall when the weather is pleasant and the crowds are thinner.

Monopoli is a 2,500-year-old whitewashed port town on Puglia's Adriatic coast, where 20 churches fill a medieval labyrinth above tiny swimming coves of crystalline water. Must-dos include the morning fish market at the old port, tasting burrata and crudo at harbour-side restaurants, and swimming at the hidden calette beaches. Visit June or September for warm seas and luminous Puglian light.

Otranto, Italy is a distinctive port city where deep cultural heritage meets authentic local atmosphere, featured on itineraries by Windstar Cruises. Must-do experiences include walking the historic center to experience the layered architectural heritage, and seeking out the regional culinary traditions at a locally favored establishment away from the port area. The optimal time to visit is May through September, when mild temperatures and long days favor unhurried exploration.

Gallipoli is a compelling Mediterranean port in Italy where centuries of history, vibrant local cuisine, and luminous coastal scenery converge. Visitors should explore the historic quarters on foot and surrender to the local dining culture, where fresh seafood and regional wines provide a masterclass in Mediterranean living. Best visited May through October, when the climate is at its most welcoming for outdoor exploration. Cruise lines including Windstar Cruises feature this port on their most compelling itineraries. Whether you have a few hours or a full day, the port rewards exploration at every pace and in every direction.

Taormina is a cliffside Sicilian jewel 200 meters above the Ionian Sea, featuring an ancient Greek theater with Mount Etna as its backdrop, the exquisite Isola Bella bay, and some of Sicily's finest cuisine. Must-dos include a performance at the Teatro Antico, the cable car to Isola Bella, and tasting Etna volcanic wines. April through June and September through October offer ideal temperatures.

Reggio di Calabria is the toe of Italy's boot, home to the magnificent Bronzi di Riace bronze warriors and a sun-drenched waterfront promenade overlooking the Strait of Messina and Sicily. Must-dos include visiting the Magna Grecia museum, tasting 'nduja and grilled swordfish, and walking the Lungomare with Mount Etna in view. May through October offers the warmest weather and calmest strait conditions.

Palermo is the Mediterranean's most intoxicating crossroads of civilisations — Arab arches meet Byzantine gold mosaics beneath Norman royal chapels in the extraordinary Palatine Chapel, a monument to 12th-century multicultural brilliance that is Sicily's single greatest work of art. The Ballarò and Capo street markets, among southern Italy's most atmospheric, tumble through the ancient city in a sensory barrage of swordfish, blood oranges, jasmine, and street food improvised across centuries. Do not leave without tasting arancini and sfincione, Sicily's gloriously thick street pizza. Spring (April–May) and autumn (September–October) offer the ideal climate — warm enough for the sea, cool enough for extended walking.